Tandem Asymmetric Conjugate Addition-Silylation of Enantiomerically Enriched Zinc Enolates. Synthetic Importance and Mechanistic Implications

Organic Letters

Volumn 4, Issue 22, 2002, Pages 3835-3837

  Knopff, Oliver ^a   Alexakis, Alexandre ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

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ARTICLE;

EID: 0344976142     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026644o     Document Type: Article

References (55)

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35. For attempted acceleration of the conjugate addition of diethylzine by TMSCl, see: (a) Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205. (b) Reddy, C. K.; Devasagayaraj, A.; Knochel, P. Tetrahedron Lett. 1996, 37, 4495. (c) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628. (d) Schinnerl, M.; Seitz, M.; Seitz, A.; Kaiser, A.; Reiser, O. Org. Lett. 2001, 3, 4259. For other examples of silylation of zinc enolates in polar media, see: (e) Nakamura, E.; Aoki, S.; Sekiya, K.; Oshhino, H.; Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056. (f) Kim, S.; Moon Lee, J. Tetrahedron Lett. 1990, 31, 7627. (g) Matsubara, S.; Arioka, D.; Utimoto, K. Synlett 1999, 1253.
36. For attempted acceleration of the conjugate addition of diethylzine by TMSCl, see: (a) Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205. (b) Reddy, C. K.; Devasagayaraj, A.; Knochel, P. Tetrahedron Lett. 1996, 37, 4495. (c) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628. (d) Schinnerl, M.; Seitz, M.; Seitz, A.; Kaiser, A.; Reiser, O. Org. Lett. 2001, 3, 4259. For other examples of silylation of zinc enolates in polar media, see: (e) Nakamura, E.; Aoki, S.; Sekiya, K.; Oshhino, H.; Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056. (f) Kim, S.; Moon Lee, J. Tetrahedron Lett. 1990, 31, 7627. (g) Matsubara, S.; Arioka, D.; Utimoto, K. Synlett 1999, 1253.
37. For attempted acceleration of the conjugate addition of diethylzine by TMSCl, see: (a) Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205. (b) Reddy, C. K.; Devasagayaraj, A.; Knochel, P. Tetrahedron Lett. 1996, 37, 4495. (c) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628. (d) Schinnerl, M.; Seitz, M.; Seitz, A.; Kaiser, A.; Reiser, O. Org. Lett. 2001, 3, 4259. For other examples of silylation of zinc enolates in polar media, see: (e) Nakamura, E.; Aoki, S.; Sekiya, K.; Oshhino, H.; Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056. (f) Kim, S.; Moon Lee, J. Tetrahedron Lett. 1990, 31, 7627. (g) Matsubara, S.; Arioka, D.; Utimoto, K. Synlett 1999, 1253.
38. For attempted acceleration of the conjugate addition of diethylzine by TMSCl, see: (a) Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205. (b) Reddy, C. K.; Devasagayaraj, A.; Knochel, P. Tetrahedron Lett. 1996, 37, 4495. (c) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628. (d) Schinnerl, M.; Seitz, M.; Seitz, A.; Kaiser, A.; Reiser, O. Org. Lett. 2001, 3, 4259. For other examples of silylation of zinc enolates in polar media, see: (e) Nakamura, E.; Aoki, S.; Sekiya, K.; Oshhino, H.; Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056. (f) Kim, S.; Moon Lee, J. Tetrahedron Lett. 1990, 31, 7627. (g) Matsubara, S.; Arioka, D.; Utimoto, K. Synlett 1999, 1253.
39. For attempted acceleration of the conjugate addition of diethylzine by TMSCl, see: (a) Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205. (b) Reddy, C. K.; Devasagayaraj, A.; Knochel, P. Tetrahedron Lett. 1996, 37, 4495. (c) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628. (d) Schinnerl, M.; Seitz, M.; Seitz, A.; Kaiser, A.; Reiser, O. Org. Lett. 2001, 3, 4259. For other examples of silylation of zinc enolates in polar media, see: (e) Nakamura, E.; Aoki, S.; Sekiya, K.; Oshhino, H.; Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056. (f) Kim, S.; Moon Lee, J. Tetrahedron Lett. 1990, 31, 7627. (g) Matsubara, S.; Arioka, D.; Utimoto, K. Synlett 1999, 1253.
40. For attempted acceleration of the conjugate addition of diethylzine by TMSCl, see: (a) Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205. (b) Reddy, C. K.; Devasagayaraj, A.; Knochel, P. Tetrahedron Lett. 1996, 37, 4495. (c) Chataigner, I.; Gennari, C.; Ongeri, S.; Piarulli, U.; Ceccarelli, S. Chem. Eur. J. 2001, 7, 2628. (d) Schinnerl, M.; Seitz, M.; Seitz, A.; Kaiser, A.; Reiser, O. Org. Lett. 2001, 3, 4259. For other examples of silylation of zinc enolates in polar media, see: (e) Nakamura, E.; Aoki, S.; Sekiya, K.; Oshhino, H.; Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056. (f) Kim, S.; Moon Lee, J. Tetrahedron Lett. 1990, 31, 7627. (g) Matsubara, S.; Arioka, D.; Utimoto, K. Synlett 1999, 1253.
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49. This is in contrast to the (Z)-selectivity (96:4) observed when the ketone is reacted with TMSCl and triethylamine. See ref 20.
50. 2O, a mixture of four enol ethers was obtained with a (Z)-selectivity for the minor regioisomers (E)-5/(Z)-5 = 4/96. (Matrix Presented)
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55. 2O.